New efficient design and synthesis of novel antioxidant and antifungal 7-imino[1,3]selenazolo[4,5-d]pyrimidine-5(4H)-thiones utilizing a base-promoted cascade addition/cyclization sequence

Sheikhi‐Mohammareh, Seddigheh; Shiri, Ali; Beyzaei, Hamid; Yarmohammadi, Elahe

doi:10.1007/s00706-020-02617-2

Cited by 13 publications

(2 citation statements)

References 64 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Whether these relative high drug concentrations can be achieved in vivo remains to be established. A straightforward strategy for the efficient synthesis of multi-functionalized 7-imino[1,3] selenazolo [4,5-d]pyrimidine-5(4H)-thiones 52 was described by Yarmohammadi and coworkers [80]. The target compounds were obtained by the incorporation of the N-phenylmethanethioamide fragment through the heteroannulation of several 2,4,5-trisubstituted 1,3-selenazoles 50.…”

Section: Se-functionalized N-heterocyclesmentioning

confidence: 99%

Recent Advances in the Synthesis and Antioxidant Activity of Low Molecular Mass Organoselenium Molecules

Anghinoni,

Birmann,

da Rocha

et al. 2023

Molecules

View full text Add to dashboard Cite

Selenium is an essential trace element in living organisms, and is present in selenoenzymes with antioxidant activity, like glutathione peroxidase (GPx) and thioredoxin reductase (TrxR). The search for small selenium-containing molecules that mimic selenoenzymes is a strong field of research in organic and medicinal chemistry. In this review, we review the synthesis and bioassays of new and known organoselenium compounds with antioxidant activity, covering the last five years. A detailed description of the synthetic procedures and the performed in vitro and in vivo bioassays is presented, highlighting the most active compounds in each series.

show abstract

Section: Se-functionalized N-heterocyclesmentioning

confidence: 99%

Recent Advances in the Synthesis and Antioxidant Activity of Low Molecular Mass Organoselenium Molecules

Anghinoni,

Birmann,

da Rocha

et al. 2023

Molecules

View full text Add to dashboard Cite

show abstract

“…On the basis of the ease of access to vinamidinium salts as fascinating precursors and due to our abiding interest in synthesis of potentially bioactive heterocyclic scaffolds [27][28][29][30][31][32][33][34][35], we have continued to explore the synthetic utility of these salts for the synthesis of novel 5-bromo-4-methyl-6-pyrazolylpyrimidines appended with various secondary amine substituents. To diverse antimicrobial libraries, their antibacterial and antifungal capacities were assessed against nine pathogenic strains.…”

mentioning

confidence: 99%

Synthesis and antimicrobial/antioxidant evaluation of novel pyrimidine-based derivatives with pendant pyrazoles using vinamidinum salts

Maghamifar

Sheikhi‐Mohammareh

Shiri

et al. 2023

Preprint

Self Cite

View full text Add to dashboard Cite

Synthesis of a variety of 5-bromo-4-methyl-2-substituted pyrimidines endowed with pyrazolyl appended in C4 position is described via treatment of 5-bromo-4-hydrazineyl-6-methyl-2-substituted pyrimidines (6a–f) and vinamidinum salt of (E)-N-(3-(dimethylamino)-2-phenylallylidene)-N-methylmethanaminium perchlorate (5) in good to excellent yields. The inhibitory and hydrogen-atom donating abilities of the synthesized products were assessed against nine pathogens including six bacterial strains (both Gram-negative and Gram-positive), three fungal strains and DPPH free radicals. Notable antioxidant properties were not observed with the products. The inhibition zone diameters were determined in the range of 10.51–18.44 mm via Kirby-Bauer disk diffusion method. 5-Bromo-4-methyl-6-pyrazolylpyrimidine (7e) containing 2-(4-methylpiperazin) substituent showed the best antioxidant and antimicrobial effects. It was effective on all the tested microbial strains except Staphylococcus epidermidis. All the synthesized pyrazolyl pyrimidines, especially (7e) can be used to disinfect the environment and treat infectious diseases.

show abstract

Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents

et al. 2020

Self Cite

View full text Add to dashboard Cite

A number of diversely functionalized derivatives of a novel [1,3]selenazolo[4,5‐d]pyrimidine have been synthesized through heterocyclization of some 2,4,5‐trisubstituted‐1,3‐selenazoles with orthoesters in refluxing acetic acid. The synthetic compounds were evaluated for their antimicrobial activity against a panel of microorganisms including Gram‐negative bacteria, Gram‐positive bacteria, and pathogenic fungi. The antifungal results revealed that the new selenium‐containing heterocycles were as good as or sometimes better than terbinafine and fluconazole. The in vitro anticancer activities of aforementioned heterocyclic compounds were screened against human breast carcinoma MCF‐7 and HeLa cervical cancer cells as well as HDF (human dermal fibroblast) normal cells. Antiproliferative results indicated that compounds with piperidine moiety on MCF‐7 cells and with morpholine moiety on HeLa cells exhibited well broad‐spectrum of anticancer activities with 397, 298 and 235 μM and 533, 390 and 204 μM of IC50 values after 24, 48 and 72 h of treatments, respectively, while they had no significant toxic effects on normal cells.

show abstract

New efficient design and synthesis of novel antioxidant and antifungal 7-imino[1,3]selenazolo[4,5-d]pyrimidine-5(4H)-thiones utilizing a base-promoted cascade addition/cyclization sequence

Cited by 13 publications

References 64 publications

Recent Advances in the Synthesis and Antioxidant Activity of Low Molecular Mass Organoselenium Molecules

Recent Advances in the Synthesis and Antioxidant Activity of Low Molecular Mass Organoselenium Molecules

Synthesis and antimicrobial/antioxidant evaluation of novel pyrimidine-based derivatives with pendant pyrazoles using vinamidinum salts

Synthesis of Various Derivatives of [1,3]Selenazolo[4,5‐d]pyrimidine and Exploitation of These Heterocyclic Systems as Antibacterial, Antifungal, and Anticancer Agents

Contact Info

Product

Resources

About